Field of the Invention
The present application discloses compounds and monomers having a carbonate linkage. The monomers can be used to form homopolymers or can be coupled with other monomers to provide a wide variety of non-homopolymers. The present application further provides a wide variety of compositions comprising the compounds, monomers, and polymers.
Description of Related Art
U.S. Pat. No. 5,210,332 discloses a process for preparing ethers which comprises contacting a carboxylated ether with a metal oxide catalyst under conditions effective to produce the ether.
U.S. Pat. No. 4,954,553 discloses waterborne phenoxy resins which are blended with modifier resins.
U.S. Pat. No. 3,377,316 discloses polyhydroxyaminoureas of the formula:
wherein Z is a 1,4-piperazine diradical (1,4-piperazinylene radical), E is a hydroxyl containing radical residuum of an epoxide, and m is an integer from 1 to 2.
U.S. Pat. No. 4,237,250 discloses polyurethanes containing sulfonic acid ester groups, characterized by aryl sulfonic acid alkyl ester groups attached to aromatic nuclei as chain members.
U.S. Pat. No. 3,821,160 discloses thermoplastic polyhydroxy-ethers having improved stress-crack resistance properties. The “thermoplastic polyhydroxy-ethers” are disclosed to be substantially liner polymers having the general formula:
wherein D is the radical residuum of a dihydric phenol, E is a hydroxyl containing radical residuum of an epoxide, and n represents the degree of polymerization and is at least 30 and is preferably 80 or more.
U.S. Pat. No. 2,795,572 discloses epoxy-substituted organic compounds, more particularly, epoxy-esters of carbonic acids, methods of preparation thereof, and utilization of the esters, particularly as stabilizers and plasticizers, and as monomers for the preparation of improved polymeric products.
U.S. Pat. No. 5,159,098 discloses alk-1-enyloxy carbamates which are rapidly curable by cationic radiation, and the use of these products as protective coatings, reactive diluents for other polymerizable compounds, and as photoresist materials.
A process for preparation of cyclic carbonates by reaction of alkali metal carbonates with epihalohydrins is described by Gabriel Rokicki and Witold Kuran in Bulletin of Chemical Society of Japan, 1984, 57, 1662-1666.
Degradable compounds, monomers, and polymers are substances that can be degraded in a biological or non-biological environment. Because of the increasing use of polymers in disposable items, drug delivery systems, and tissue regeneration scaffolds, there is a need for compounds, monomers, and polymers that are degradable.
Methods to develop degradable polymers include modifying existing degradable monomers to add functionality to provide desirable properties. A useful degradable functional group is the carbonate linkage,
Carbonate linkages in organic compounds, such as carbonate esters, can be employed as degradable functional groups because they can be converted to carbon dioxide. The carbonate linkage, or group, can be introduced into a compound through the use of the coupling agent 1,1′-carbonyldiimidazole (CDI):

1,1′-Carbonyldiimidazole is a useful coupling agent because it is very reactive towards nucleophiles. The coupling ability of 1,1′-carbonyldiimidazole may be used to prepare degradable compounds containing a carbonate linkage.
The degradable monomers contain a carbonate linkage that can be used to form homopolymers or can be coupled with other monomers to provide, through the use of polymerization initiators, a wide variety of functionalized polymers.
Modification of degradable compounds with various functional groups can provide polymers having different physical or mechanical properties useful in a wide variety of compositions. The resulting modification of the physical or mechanical properties will depend upon the nature of the functional group and/or mixture of functional groups. Accordingly, there is a need for degradable polymers, resulting from modification of degradable compounds, to alter or improve the physical and mechanical properties of such degradable polymers.